Reaction #1178453

Reaction equation

4-methylmorpholine

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

(R)-2-(4-chlorophenyl-carbamoyl)pyrrolidinium chloride

4-(3-oxomorpholin-4-yl)phenylacetic acid

→

N-(4-chlorophenyl)-(R)-1-{2-[4-(3-oxomorpholin-4-yl)phenyl]acetyl}pyrrolidine-2-carboxamide

Solvents

water

DMF

Conditions

Workup

1. 1
   Otherthe precipitate formed
2. 2
   Filtrationis filtered off

Procedure

0.26 ml (2.4 mmol) of 4-methylmorpholine and 230 mg (1.2 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (DAPECI) are added to a solution of 261 mg (1.00 mmol) of (R)-2-(4-chlorophenyl-carbamoyl)pyrrolidinium chloride and 235 mg (1.00 mmol) of 4-(3-oxomorpholin-4-yl)phenylacetic acid in 2 ml of DMF, and the mixture is stirred at room temperature for 18 hours. The reaction mixture is introduced into water, and the precipitate formed is filtered off, giving N-(4-chlorophenyl)-(R)-1-{2-[4-(3-oxomorpholin-4-yl)phenyl]acetyl}pyrrolidine-2-carboxamide as a slightly brownish solid; ESI 442.

Source